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The Gambling Cowboy

The Gambling Cowboy The Gambling Cowboy is a steakhouse and American restaurant located on 5th Street in the heart of Old Town Temecula, CA. Offering a top-notch dining experience, customers can choose to sit on the third-floor balcony for unparalleled views or cozy up in the saloon and sample a variety of dishes such as Grilled Artichoke, Street Tacos, and 8oz. Top Sirloin Steak & Fries. Known for their delicious steaks and seafood, The Gambling Cowboy is a must-visit destination for any foodie.
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Recent social media posts

Closed Today See You Wednesday!
06/02/2026

Closed Today See You Wednesday!

Celebrating Mom !!The Gambling Cowboy
05/09/2026

Celebrating Mom !!
The Gambling Cowboy

Join us this Cinco de Mayo 🌮🔥All your Cowgirl Cantina favorites, all day—street tacos, chilaquiles, ribeye relleno and m...
05/05/2026

Join us this Cinco de Mayo 🌮🔥
All your Cowgirl Cantina favorites, all day—street tacos, chilaquiles, ribeye relleno and more.

$5 drafts & house margaritas flowing all day. Come hungry and celebrate with us!

Love our people!!
05/02/2026

Love our people!!

Hiring all front of the house staff!Minimum 2-year high volume restaurant experience required, 18+ due to alcohol regula...
04/22/2026

Hiring all front of the house staff!

Minimum 2-year high volume restaurant experience required, 18+ due to alcohol regulations

Grab your peeps and join us this Thursday for the Spring Boutique Crawl.Try our Easter Blushing Bunny Spritz; A bright, ...
03/30/2026

Grab your peeps and join us this Thursday for the Spring
Boutique Crawl.

Try our Easter Blushing Bunny Spritz; A bright, bubbly spring cocktail with raspberry, fresh citrus and touch of smoke. Garnished with a peep!

Great deal on brie as well!!

Easter weekend is almost here 🐣🌸Our special menu is locked in and reservations are filling up fast.Brunch, lunch, and di...
03/29/2026

Easter weekend is almost here 🐣🌸
Our special menu is locked in and reservations are filling up fast.

Brunch, lunch, and dinner all weekend—come celebrate with us 🥂
Reserve your table now before we’re fully booked!

Easter is just around the corner!
03/18/2026

Easter is just around the corner!

Valentine’s Day is pretty close to full. We will be serving Valentine’s specials all day, all week, with local floral bo...
01/27/2026

Valentine’s Day is pretty close to full. We will be serving Valentine’s specials all day, all week, with local floral bouquet add-ons from available. We would love to see you there! 💕

Don’t miss your chance. Reserve now!

Cozy up. Have a glass with us.We’ll take care of dinner.
01/10/2026

Cozy up. Have a glass with us.
We’ll take care of dinner.

Live music is back and we’re stacking the weekend 🎸Thursday 6–9pm: Virginia JamesFriday 6–9pm: The LookoutsSaturday 6–9p...
01/07/2026

Live music is back and we’re stacking the weekend 🎸
Thursday 6–9pm: Virginia James
Friday 6–9pm: The Lookouts
Saturday 6–9pm: Dustin Jake
Cold drinks, good sounds, and the room full again.
Pull up. 🤠🎶

🥂 Happy New Year from all of us at The Gambling Cowboy!We’re giving our hardworking Cowboys and Cowgirls a little breath...
01/01/2026

🥂 Happy New Year from all of us at The Gambling Cowboy!

We’re giving our hardworking Cowboys and Cowgirls a little breather — closed Jan 1st–5th.
Thank you for riding with us through an amazing 2025 — your laughter, cheers, and support made it unforgettable. 🧡

We can’t wait to see you back on Jan 6! Make your reservations online and let’s kick off the new year together. 🥩✨

✨ Ring in the New Year at The Gambling Cowboy ✨Celebrate New Year’s New York–style at Temecula’s Original Steakhouse & S...
12/28/2025

✨ Ring in the New Year at The Gambling Cowboy ✨
Celebrate New Year’s New York–style at Temecula’s Original Steakhouse & Saloon.
🕰 Saloon Opens: 2 PM
🍽 Dinner Begins: 3 PM
🎉 East Coast Celebration: 6–10 PM
⏰ Midnight Countdown: 9 PM (East Coast Time)
🎟 Cover: $65 per person
Food & beverage not included
Start the evening with a juicy steak and fresh seafood, then try your luck at our Blackjack speakeasy, capture the moment in our glamorous photo booth, indulge at the oyster bar, and toast with a complimentary split of champagne.
🎶 Live music by Gennine Francis & Company keeps the celebration going all night.
🥂 New Year. New Memories. The Gambling Cowboy

Celebrate New Year’s in style at Temecula’s original steakhouse & saloon. Enjoy prime steaks, fresh seafood, live music ...
12/24/2025

Celebrate New Year’s in style at Temecula’s original steakhouse & saloon. Enjoy prime steaks, fresh seafood, live music by Gennine Francis and Company, a speakeasy blackjack experience, oysters, and a complimentary champagne toast. East Coast countdown at 9 PM.

We hope to ring in the New Year with you! 🥂

12/13/2025

Ready to pop into the holidays 🍾✨
The crew’s ready to see you 🎄
And if you haven’t yet — try our White Winter Martini 🍸
Literally like a melted milkshake. So good 🤍

Prime steaks. Fresh-caught seafood. Serving Old Town for 16 years. Classic flavors, legendary atmosphere—you keep coming...
12/12/2025

Prime steaks. Fresh-caught seafood. Serving Old Town for 16 years. Classic flavors, legendary atmosphere—you keep coming back for a reason.
starts at 7 — see you tonight.

WINTER BOUTIQUE CRAWL ❄️ — DEC 11 · 11AM–7PMGrab your stamp card at your first stop and collect stamps as you shop your ...
12/09/2025

WINTER BOUTIQUE CRAWL ❄️ — DEC 11 · 11AM–7PM
Grab your stamp card at your first stop and collect stamps as you shop your way through Old Town! Unlock exclusive deals, giveaways, and surprises at every boutique.
✨ OUR CRAWL SPECIALS:
• $10 White Winter Martini
• $10 Crab & Shrimp Cake
(Show the coupon to redeem!)
ENTER TO WIN 🎁
Get 5+ shopping stamps & 5+ visiting stamps, then drop your card at your last stop to enter for a $250+ Old Town gift basket.

Look for winter balloons, Crawl shirts, stamp stations, and free winter totes while supplies last!
See you in Old Town! ❄️🛍️🍸

Hey everyone, the restaurant’s officially decked out! Come on by and enjoy the holiday feel. ❄️❤️
12/09/2025

Hey everyone, the restaurant’s officially decked out! Come on by and enjoy the holiday feel. ❄️❤️

Address

42072 5th Street, Fl 3rd
Temecula, CA
92590

To get to 5th Street in Temecula, there are a few options for public transportation. You can take the bus and get off at one of the stops along the street, such as Jefferson Ave & 5th St or Old Town Front St & 5th St. Alternatively, you can take a ride-sharing service like Uber or Lyft to drop you off directly on the street.

If you are driving, there is street parking available along 5th Street. You may also find parking in nearby lots or garages off of 5th Street. Just be sure to check any posted signs for restrictions or time limits.

Once you arrive on 5th Street, look for The Gambling Cowboy restaurant which is situated somewhere along the street.

Opening Hours

Tuesday 11am - 9pm
Wednesday 11am - 9pm
Thursday 11am - 9pm
Friday 11am - 11pm
Saturday 9am - 11pm
Sunday 9am - 9pm

Telephone

+19516992895

Website

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What people say

The Gambling Cowboy on 5th Street in Temecula is a must-visit for anyone looking for a top-notch dining experience. This steakhouse and American restaurant offers both fine dining and a cozy saloon atmosphere, making it the perfect spot for any occasion.

One of the highlights of The Gambling Cowboy is its third-floor balcony, which offers stunning views of Old Town Temecula. It's the perfect place to enjoy a romantic dinner or celebrate a special occasion with friends and family.

But even if you're not in the mood for fine dining, The Gambling Cowboy has you covered with its saloon menu. From Grilled Artichoke to Street Tacos to an 8oz. Top Sirloin Steak & Fries, there's something for everyone on this menu.

No matter what you choose to order, you can be sure that everything at The Gambling Cowboy is made with the highest quality ingredients and prepared with care by skilled chefs. So if you're looking for a memorable dining experience in Temecula, look no further than The Gambling Cowboy on 5th Street.

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